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WO2016107459A1 - Compositions comprenant des indoles 2, 3-disubstitués comme matériaux de transport de charge, et dispositifs d'affichage fabriqués à partir de celles-ci - Google Patents

Compositions comprenant des indoles 2, 3-disubstitués comme matériaux de transport de charge, et dispositifs d'affichage fabriqués à partir de celles-ci Download PDF

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Publication number
WO2016107459A1
WO2016107459A1 PCT/CN2015/098252 CN2015098252W WO2016107459A1 WO 2016107459 A1 WO2016107459 A1 WO 2016107459A1 CN 2015098252 W CN2015098252 W CN 2015098252W WO 2016107459 A1 WO2016107459 A1 WO 2016107459A1
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Prior art keywords
layer
compound
composition
group
hydrocarbyl
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English (en)
Inventor
Kaitlyn Gray
Robert Wright
Liam SPENCER
David Devore
David Pearson
Ji Chang FENG
Jing Jing YAN
Shao Guang FENG
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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Priority to KR1020177018722A priority Critical patent/KR20170100552A/ko
Priority to EP15875137.0A priority patent/EP3240776A4/fr
Priority to CN201580068921.4A priority patent/CN107406382A/zh
Priority to US15/539,856 priority patent/US9966537B2/en
Publication of WO2016107459A1 publication Critical patent/WO2016107459A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • OLEDs are light-emitting diodes (LEDs) , which include an emissive electroluminescent layer composed of an organic compound that emits light in response to an electric current.
  • a typical OLED has a multi-layer structure, and typically includes an indium tin oxide (ITO) anode and a metal cathode. Sandwiched between the anode and cathode are several organic layers, such as a hole injection layer (HIL) , a hole transport (or transfer) layer (HTL) , an emitting material layer (EML) , an electron transport (or transfer) layer (ETL) , an electron injection layer (EIL) , and a hole blocking layer.
  • HIL hole injection layer
  • HTL hole transport
  • EML emitting material layer
  • ETL electron transport (or transfer) layer
  • EIL electron injection layer
  • EIL electron injection layer
  • HTLs hole transport layers
  • the state of the art technology uses triarylamine-based materials to satisfy many of the current luminescent and phosphorescent OLED designs. Problems with current OLEDs include fast aging/short life span, undesirably high operating voltages, low efficiency and low levels of brightness. There remains a need for new HTL materials for OLED applications.
  • the invention provides a composition comprising a compound of Structure 1:
  • R 1 through R 24 are each, independently, selected from the following: a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, or a NR' 2 wherein R' is selected from an aryl or a heteroaryl; and
  • R 1 to R 24 form one or more ring structures
  • Z is selected from group (1) or (2) :
  • the invention further provides a film formed from a composition comprising at least one compound of Structure 1, and an electronic device comprising at least one component formed from a composition or from a film comprising at least one compound of Structure 1.
  • the invention also provides a composition comprising a compound of Structure 2:
  • R 1 through R 24 are each, independently, selected from the following: a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, or a NR' 2 wherein R' is selected from an aryl or a heteroaryl; and
  • R 1 to R 24 form one or more ring structures
  • Z is selected from group (1a) or (2a) :
  • Ra and Rb are each independently an alkyl, and wherein at least one of Ra and/or Rb comprises at least two carbon atoms; and for group 2a, Rc and Rd are each independently an alkyl, and wherein at least one of Rc and/or Rd comprises at least two carbon atoms; and
  • Figure 1 depicts the cyclic voltammetry profiles of a model compound (9- (4- (2, 3-dimethyl-1H-indol-1-yl) phenyl) -9H-carbazole) , used to determine the stability of the Z moiety, as noted in the "stability study" below.
  • a new class of 2, 3-disubstituted indole compounds have been discovered that are highly stable and useful in OLEDs and other electroluminescent (EL) display devices, particularly as charge transport materials (e.g., HTL and ETL materials) .
  • EL electroluminescent
  • Electroluminescent (EL) display devices incorporating these compounds exhibit good electroluminescent performance.
  • composition comprising a compound selected from Structure 1:
  • R 1 through R 24 are each, independently, selected from a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, and a NR' 2 wherein R' is selected from an aryl or a heteroaryl;
  • R 1 to R 24 form one or more ring structures
  • Z is selected from group (1) or (2) :
  • the compound of Structure 1 can comprise a combination of two or more embodiments as described herein.
  • An inventive composition may comprise a combination of two or more embodiments described herein.
  • NR'2 NR' 2 .
  • R1 through R24 are each, independently, selected from a hydrogen, a C1-C20 hydrocarbyl, a substituted C1-C20 hydrocarbyl, a cyano, a C1-C20 alkoxy, a C6-C18 aryloxy, or an NR' 2 group with the R' group selected from a C6-C18 aryl or a C3-C18 heteroaryl.
  • R 1 through R 24 are each independently selected from the following: hydrogen, an unsubstituted hydrocarbyl, or a substituted hydrocarbyl.
  • R1 through R24 are each, independently, hydrogen.
  • R groups do not form one or more ring structures.
  • one or more hydrogens are not substituted with deuterium.
  • the Z is group (1) :
  • Structure 1 is Structure 1a:
  • Z is group (2) :
  • Structure 1 is Structure 2a:
  • the compound of Structure 1 comprises at least one deuterium atom.
  • the compound of Structure 1 does not comprise a deuterium atom.
  • the compound of Structure 1 has a purity greater than 99 percent (%) as determined by analytical methods, for example, high-performance liquid chromatography (HPLC) , liquid chromatography (LC) , and/or liquid chromatography–mass spectrometry (LC-MS or HPLC-MS) .
  • HPLC high-performance liquid chromatography
  • LC liquid chromatography
  • HPLC-MS liquid chromatography–mass spectrometry
  • the compound of Structure 1 has a glass transition temperature (Tg) from 90 to 200°C, further from 100 to 180°C, further from 110 to 180°C, as determined by DSC.
  • Tg glass transition temperature
  • the compound of Structure 1 has a molecular weight of 600 grams/mole (g/mole) to 1000 g/mole, further from 600 to 900 g/mole, further from 700 to 900 g/mole.
  • the compound of Structure 1 has a highest occupied molecular orbital (HOMO) level of from -4.40 eV to -5.00 eV, further from -4.50 eV to -4.90 eV.
  • HOMO highest occupied molecular orbital
  • the compound of Structure 1 has a lowest unoccupied molecular orbital (LUMO) level from -1.00 eV to 0.00 eV, further from –0.90 eV to –0.20 eV, further from -0.90 eV to -0.40 eV.
  • LUMO lowest unoccupied molecular orbital
  • the compound of Structure 1 has a triplet energy level from 2.50 eV to 3.00 eV, further from 2.55 eV to 2.90 eV, further 2.60 eV to 2.80 eV.
  • the composition comprises at least two compounds of Structure 1.
  • the composition comprises at least one compound of Structure 1 in which Z is group (1) and at least one compound of Structure 1 in which Z is group (2) .
  • the composition consists essentially of a compound of Structure 1 in which Z is group (1) .
  • the composition consists essentially of a compound of Structure 1 in which Z is group (2) .
  • the Z group of group 1 when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ⁇ 3.0 x 10 -5 A, for at least 2, further at least 3, further at least 4, and further at least 5 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.
  • the difference in amperage (A) between each voltage point (V) is within ⁇ 3.0 x 10 -5 A. See the experimental section below for a representative cyclic voltammetry measurement, and Figure 1 for representative cyclic voltammograms (or cyclic voltammetry profiles) .
  • the Z group of group 1 when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ⁇ 2.5 x 10 -5 A, for at least 2, further at least 3, further at least 4, and further at least 5 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.
  • the Z group of group 1 when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ⁇ 2.0 x 10 -5 A, for at least 2, further at least 3, further at least 4, and further at least 5 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.
  • the Z group of group 1 when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ⁇ 1.5 x 10 -5 A, for at least 2, further at least 3, further at least 4, and further at least 5 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.
  • the Z group of group 1 when attached to a carbazole via the nitrogen atom of the carbazole, provides an electrochemical stability within ⁇ 1.0 x 10 -5 A, for at least 2, further at least 3, further at least 4, and further at least 5 repeated cyclic voltammograms, each with a voltage range from 1.6 V to 0 V.
  • the composition is 100 weight percent (wt%) of the compound of Structure 1, based on the weight of the composition. In a further embodiment, the composition comprises from 10 to 99 wt%of the compound of Structure 1, based on the weight of the composition. In a further embodiment, the composition comprises from 50 to 99 wt%, further from 70 to 99 wt%, further from 80 to 99 wt%, further from 90 to 99 wt%, of the compound of Structure 1, based on the weight of the composition.
  • the inventive composition can comprise a combination of two or more embodiments as described herein.
  • the present disclosure also provides an inventive film comprising at least one layer formed from an inventive composition comprising a compound of Structure 1, including an inventive composition of one or more embodiments described herein.
  • the film comprises at least two layers, A and B, wherein the Layer A is formed from a composition A comprising a compound of Structure 1.
  • the Layer A formed from the inventive composition can comprise a combination of two or more embodiments described herein.
  • the Layer A is in contact with the Layer B.
  • the thickness of Layer A is from 5 nm to 500 nm, or from 5 nm to 100 nm, or from 5 nm to 50 nm.
  • the Layer A is a hole transport layer (HTL) .
  • HTL hole transport layer
  • the Layer A is a hole transport layer (HTL) formed from a composition comprising a compound of Structure 1, which compound is a hole transport layer (HTL) compound.
  • HTL hole transport layer
  • an HTL compound is a material that transports holes.
  • An HTL compound of Structure 1 should desirably have a larger triplet energy than the EML layer to block exciton migration from an adjacent emitting material layer (EML) .
  • the inventive composition can comprise 100 wt%of a hole transport layer (HTL) compound of Structure 1, based on the weight of the composition.
  • HTL hole transport layer
  • the inventive composition comprising a hole transport layer (HTL) compound of Structure 1 can comprise a combination of two or more embodiments described herein.
  • the inventive film is formed from casting from a solution.
  • the inventive film is formed by deposition from an evaporation process or a sublimation process in a vacuum.
  • the film comprises a hole transport layer (HTL) as Layer A and one or more additional layers selected from a hole injection layer (HIL) , an emitting material layer (EML) , an electron transport layer (ETL) , or an electron injection layer (EIL) .
  • HIL hole injection layer
  • EML emitting material layer
  • ETL electron transport layer
  • EIL electron injection layer
  • each film layer is formed from casting from a solution.
  • each film layer is formed by deposition from an evaporation process or a sublimation process in a vacuum.
  • An inventive film can comprise a combination of two or more embodiments described herein.
  • the present disclosure also provides an electronic device comprising at least one component formed from an inventive composition, including an inventive composition of one or more embodiments described herein.
  • the present disclosure also provides an electronic device comprising at least one component formed from an inventive film, including an inventive film of one or more embodiments described herein.
  • the device is a light-emitting or electroluminescent (EL) device.
  • EL electroluminescent
  • the electronic device comprises an organic material layer disposed between first and second electrodes (e.g., anode and cathode) .
  • the electronic device comprises at least one component formed from the inventive composition.
  • the electronic device comprises an organic Layer A formed from the inventive composition disposed between first and second electrodes.
  • the electronic device further comprises a second Layer B.
  • the Layer A is in contact with the Layer B.
  • the Layer A of the electronic device is a hole transport layer (HTL) .
  • HTL hole transport layer
  • the organic material layer of the electronic device comprises at least one of an HIL (hole injection layer) , an HTL (hole transport layer) , an EML (emissive material layer) , and an ETL (electron transport layer) .
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emissive material layer
  • ETL electron transport layer
  • the organic material layer further includes a hole-blocking layer to improve efficiency of phosphorescent emitter devices.
  • the electronic device is an organic light emitting diode (OLED) .
  • the electronic device is an OLED comprising an organic material layer comprising an inventive film disposed between two electrodes (anode and cathode) .
  • the OLED device comprises a multi-layered organic material layer with one or more layers selected from an HIL (hole injection layer) , an HTL (hole transport layer) , an EML (emissive layer) , an ETL (electron transport layer) , or an EIL (electron injection layer) , of which at least one layer is formed from an inventive composition comprising a compound of Structure 1.
  • An inventive device may comprise a combination of two or more embodiments as described herein.
  • inventive compositions are useful for application in organic light emitting diodes (OLED) or related organic electronic devices, including organic solar cells. More specifically, the invented compositions find application in individual layers of OLEDs, including HIL (hole injection layers) , HTL (hole transport layers) , EML (emissive layers, including host and dopant) , EIL (electron injection layers) , and ETL (electron transport layers) .
  • HIL hole injection layers
  • HTL hole transport layers
  • EML emissive layers, including host and dopant
  • EIL electron injection layers
  • ETL electrostatic transport layers
  • the invention also provides A composition comprising a compound of Structure 2:
  • R 1 through R 24 are each, independently, selected from the following: a hydrogen, a hydrocarbyl, a substituted hydrocarbyl, a cyano, an alkoxy, an aryloxy, or a NR' 2 wherein R' is selected from an aryl or a heteroaryl; and
  • R 1 to R 24 form one or more ring structures
  • Z is selected from group (1a) or (2a) :
  • Ra and Rb are each independently an alkyl, and at least one of Ra and/or Rb comprises at least two carbon atoms; and for group 2a, Rc and Rd are each independently an alkyl, and wherein at least one of Ra and/or Rb comprises at least two carbon atoms; and
  • each of Ra and Rb independently is a C2-C6 alkyl, further a C2-C5 alkyl and further a C2-C4 alkyl; and each of Rc and Rd, independently is a C2-C6 alkyl, further a C2-C5 alkyl and further a C2-C4 alkyl.
  • the compound of Structure 2 comprises at least one deuterium atom.
  • the compound of Structure 2 does not comprise a deuterium atom.
  • the compound of Structure 2 has a purity greater than 99 percent (%) as determined by analytical methods, for example, high-performance liquid chromatography (HPLC) , liquid chromatography (LC) , and/or liquid chromatography–mass spectrometry (LC-MS or HPLC-MS) .
  • HPLC high-performance liquid chromatography
  • LC liquid chromatography
  • HPLC-MS liquid chromatography–mass spectrometry
  • the compound of Structure 2 has a glass transition temperature (Tg) from 90 to 200°C, further from 100 to 180°C, further from 110 to 180°C, as determined by DSC.
  • Tg glass transition temperature
  • the compound of Structure 2 has a molecular weight of 600 grams/mole (g/mole) to 1000 g/mole, further from 600 to 900 g/mole, further from 700 to 900 g/mole.
  • the compound of Structure 2 has a highest occupied molecular orbital (HOMO) level of from -4.40 eV to -5.00 eV, further from -4.50 eV to -4.90 eV.
  • HOMO highest occupied molecular orbital
  • the compound of Structure 2 has a lowest unoccupied molecular orbital (LUMO) level from -1.00 eV to 0.00 eV, further from –0.90 eV to –0.20 eV, further from -0.90 eV to -0.40 eV.
  • LUMO lowest unoccupied molecular orbital
  • the compound of Structure 2 has a triplet energy level from 2.50 eV to 3.00 eV, further from 2.55 eV to 2.90 eV, further 2.60 eV to 2.80 eV.
  • the composition comprises at least two compounds of Structure 2.
  • the composition comprises a compound of Structure 2 and a compound of Structure 1.
  • the composition comprises at least one compound of Structure 2 in which Z is group (1a) and at least one compound of Structure 2 in which Z is group (2a) .
  • the composition consists essentially of a compound of Structure 2 in which Z is group (1a) .
  • the composition consists essentially of a compound of Structure 2 in which Z is group (2a) .
  • the composition is 100 weight percent (wt%) of the compound of Structure 2, based on the weight of the composition. In a further embodiment, the composition comprises from 10 to 99 wt%of the compound of Structure 2, based on the weight of the composition. In a further embodiment, the composition comprises from 50 to 99 wt%, further from 70 to 99 wt%, further from 80 to 99 wt%, further from 90 to 99 wt%, of the compound of Structure 2, based on the weight of the composition.
  • the inventive composition can comprise a combination of two or more embodiments as described herein.
  • the present disclosure also provides an inventive film comprising at least one layer formed from an inventive composition comprising a compound of Structure 2, including an inventive composition of one or more embodiments described herein.
  • the film comprises at least two layers, C and D, wherein the Layer C is formed from a composition C comprising a compound of Structure 2.
  • the Layer C formed from the inventive composition can comprise a combination of two or more embodiments described herein.
  • the Layer C is in contact with the Layer D.
  • the thickness of Layer C is from 5 nm to 500 nm, or from 5 nm to 100 nm, or from 5 nm to 50 nm.
  • the Layer C is a hole transport layer (HTL) .
  • HTL hole transport layer
  • the Layer C is a hole transport layer (HTL) formed from a composition comprising a compound of Structure 2, which compound is a hole transport layer (HTL) compound.
  • HTL hole transport layer
  • an HTL compound is a material that transports holes.
  • An HTL compound of Structure 2 should desirably have a larger triplet energy than the EML layer to block exciton migration from an adjacent emitting material layer (EML) .
  • the inventive composition can comprise 100 wt%of a hole transport layer (HTL) compound of Structure 2, based on the weight of the composition.
  • HTL hole transport layer
  • the inventive composition comprising a hole transport layer (HTL) compound of Structure 2 can comprise a combination of two or more embodiments described herein.
  • the inventive film is formed from casting from a solution.
  • the inventive film is formed by deposition from an evaporation process or a sublimation process in a vacuum.
  • the film comprises a hole transport layer (HTL) as Layer C and one or more additional layers selected from a hole injection layer (HIL) , an emitting material layer (EML) , an electron transport layer (ETL) , or an electron injection layer (EIL) .
  • HIL hole injection layer
  • EML emitting material layer
  • ETL electron transport layer
  • EIL electron injection layer
  • each film layer is formed from casting from a solution.
  • each film layer is formed by deposition from an evaporation process or a sublimation process in a vacuum.
  • An inventive film can comprise a combination of two or more embodiments described herein.
  • the present disclosure also provides an electronic device comprising at least one component formed from an inventive composition, including an inventive composition of one or more embodiments described herein.
  • the present disclosure also provides an electronic device comprising at least one component formed from an inventive film, including an inventive film of one or more embodiments described herein.
  • the device is a light-emitting or electroluminescent (EL) device.
  • EL electroluminescent
  • the electronic device comprises an organic material layer disposed between first and second electrodes (e.g., anode and cathode) .
  • the electronic device comprises at least one component formed from the inventive composition.
  • the electronic device comprises an organic Layer C formed from the inventive composition disposed between first and second electrodes.
  • the electronic device further comprises a second Layer D.
  • the Layer C is in contact with the Layer D.
  • the Layer C of the electronic device is a hole transport layer (HTL) .
  • HTL hole transport layer
  • the organic material layer of the electronic device comprises at least one of an HIL (hole injection layer) , an HTL (hole transport layer) , an EML (emissive material layer) , and an ETL (electron transport layer) .
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emissive material layer
  • ETL electron transport layer
  • the organic material layer further includes a hole-blocking layer to improve efficiency of phosphorescent emitter devices.
  • the electronic device is an organic light emitting diode (OLED) .
  • the electronic device is an OLED comprising an organic material layer comprising an inventive film disposed between two electrodes (anode and cathode) .
  • the OLED device comprises a multi-layered organic material layer with one or more layers selected from an HIL (hole injection layer) , an HTL (hole transport layer) , an EML (emissive layer) , an ETL (electron transport layer) , or an EIL (electron injection layer) , of which at least one layer is formed from an inventive composition comprising a compound of Structure 2.
  • An inventive device may comprise a combination of two or more embodiments as described herein.
  • inventive compositions are useful for application in organic light emitting diodes (OLED) or related organic electronic devices, including organic solar cells. More specifically, the invented compositions find application in individual layers of OLEDs, including HIL (hole injection layers) , HTL (hole transport layers) , EML (emissive layers, including host and dopant) , EIL (electron injection layers) , and ETL (electron transport layers)
  • HIL hole injection layers
  • HTL hole transport layers
  • EML emissive layers, including host and dopant
  • EIL electron injection layers
  • ETL electrotron transport layers
  • the numerical ranges disclosed herein include all values from, and including, the lower value and the upper value.
  • explicit values e.g., 1 or 2, or 3 to 5, or 6, or 7
  • any subrange between any two explicit values is included (e.g., 1 to 2; 2 to 6; 5 to 7; 3 to 7; 5 to 6; etc. ) .
  • compositions claimed through use of the term “comprising” may include any additional additive, adjuvant or compound, whether polymeric or otherwise, unless stated to the contrary.
  • the term, “consisting essentially of” excludes from the scope of any succeeding recitation any other component, step or procedure, excepting those that are not essential to operability.
  • the term “consisting of” excludes any component, step or procedure not specifically delineated or listed.
  • hydrocarbon refers to a chemical group containing only hydrogen atoms and carbon atoms.
  • hydrocarbyl refers to a univalent group formed by removing a hydrogen from a hydrocarbon, such as, for example, ethyl, methyl or phenyl.
  • substituted hydrocarbon refers to a hydrocarbon (or hydrocarbyl) in which at least one hydrogen atom is substituted with a substituent comprising at least one heteroatom.
  • Heteroatoms include, but are not limited to, a halide, O, N, P and S.
  • An "unsubstituted hydrocarbon” (or “unsubstituted hydrocarbyl” ) is a hydrocarbon (or hydrocarbyl) that contains no heteroatoms.
  • alkoxy refers to an alkyl in which at least one hydrogen atom is substituted with an oxygen atom, O.
  • alkyl refers to an organic radical derived from an aliphatic hydrocarbon by deleting one hydrogen atom therefrom.
  • An alkyl group can be a linear, branched, cyclic or a combination thereof.
  • substituted alkyl refers to an alkyl, in which at least one hydrogen atom is substituted with a substituent that comprises at least one heteroatom.
  • Heteroatoms include, but are not limited to, O, N, P and S.
  • aryl refers to an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
  • An aryl group may be a monocyclic and/or fused ring system, each ring of which suitably contains from 5 to 7, preferably from 5 or 6 atoms. Structures wherein two or more aryl groups are combined through single bond (s) are also included.
  • Specific examples include, but are not limited to, phenyl, tolyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, 9, 9-dimethylfluorenyl, benzofluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl, and the like.
  • the naphthyl may be 1-naphthyl or 2-naphthyl
  • the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl
  • the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • substituted aryl refers to an aryl, in which at least one hydrogen atom is substituted with a substituent comprising at least one heteroatom.
  • Heteroatoms include, but are not limited to, O, N, P and S.
  • aryloxy refers to an aryl group in which at least one hydrogen atom is replaced with an oxygen atom, O. such as a phenoxy group (C 6 H 5 O—) .
  • cyano refers to a radical group with the molecular formula ⁇ CN, which consists of a carbon atom triple-bonded to a nitrogen atom.
  • heteroalkyl refers to an alkyl group, in which at least one carbon atom or CH group or CH 2 is substituted with a heteroatom or a chemical group containing at least one heteroatom. Heteroatoms include, but are not limited to, O, N, P and S.
  • a heteroalkyl group may be a linear, branched, cyclic or a combination thereof.
  • substituted heteroalkyl refers to an heteroalkyl, in which at least one hydrogen atom is substituted with a substituent that comprises at least one heteroatom.
  • Heteroatoms include, but are not limited to, O, N, P and S.
  • heteroaryl refers to an aryl group, in which at least one carbon atom or CH group or CH 2 is substituted with a heteroatom or a chemical group containing at least one heteroatom. Heteroatoms include, but are not limited to, O, N, P and S.
  • the heteroaryl may be a 5-or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring (s) , and may be partially saturated.
  • the structures having one or more heteroaryl group (s) bonded through a single bond are also included.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, and the like. Specific examples include, but are not limited to, monocyclic heteroaryl groups, such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups, such as benzofuranyl, fluoreno [4, 3-b] benzofuranyl, benzothiophenyl, fluoreno [4, 3-b] benzothiophenyl
  • substituted heteroaryl refers to a heteroaryl in which at least one hydrogen atom is substituted with a substituent comprising at least one heteroatom, and any combination thereof.
  • Heteroatoms include, but are not limited to, O, N, P and S.
  • a "heteroatom” is an atom other than carbon or hydrogen.
  • Nonlimiting examples of heteroatoms include: F, Cl, Br, N, O, P, B, S, Si, Sb, Al, Sn, As, Se and Ge.
  • ring structure refers to a ring composed of a hydrocarbon or a substituted hydrocarbon.
  • a ring structure can be saturated or unsaturated, and can contain one or two or more rings.
  • anode refers to a layer in an electroluminescent (EL) device that is capable of injecting positive charges (holes) into a hole injection layer (HIL) and/or hole transporting layer (HTL) , positioned thereon, when a current flows through the device.
  • EL electroluminescent
  • HIL hole injection layer
  • HTL hole transporting layer
  • the anode is typically disposed on a substrate, as for example, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet.
  • anode materials include metals (e.g., vanadium, chromium, copper, zinc, gold) or alloys thereof, metal oxides (e.g., zinc oxide, indium oxide) , metal halides, electroconductive polymers (e.g., polypyrole, polyaniline) , and combinations thereof.
  • An optically transparent anode can be formed, for example, from a transparent conductive oxide such as indium-tin-oxide (ITO) or indium zinc oxide (IZO) .
  • cathode refers to a layer in an electroluminescent (EL) device that is capable of injecting negative charges (electrons) into an electron injection layer (EIL) and/or electron transporting layer (ETL) , positioned on the electron injection layer (EIL) , when a current flows through the device.
  • the cathode can be formed, for example, from metals such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or alloys thereof.
  • An optically transparent cathode can be formed, for example, from a transparent conductive oxide such as indium-tin-oxide (ITO) or indium zinc oxide (IZO) .
  • dopant and like terms, as described herein, refer to a material that is added to an organic emissive layer, as an additive, and undergoes radiative emission from an excited state.
  • the excited state can be generated by application of electrical current in an electroluminescent device.
  • EIL electron injection layer
  • ETL electron transport layer
  • the EIL layer can be formed, for example, from a metal complex compound, such as metal chelated oxinoid compounds, triazines, and hydroxyquinoline derivatives, among others.
  • ETL electroluminescent
  • ETL electroluminescent
  • the ETL layer is composed of a material having a high electron affinity, a high electron mobility, and a high electron stability.
  • the ETL layer can be formed, for example, from anthracene-based, pyridine-based, pyrimidine-based, quinazoline-based and triazine-based compounds, among others.
  • EML electroluminescent
  • EML electroluminescent
  • HTL hole transport layer
  • ETL electron transport layer
  • the EML layer can be formed, for example, from a luminescent fluorescent material or a luminescent phosphorescent material, which can produce electroluminescence as a result of electron-hole pair recombination in the EML layer.
  • the EML layer can be composed of a host material doped with an emitting material (dopant) , where light emission comes from the dopant material, for example, a fluorescent compound or phosphorescent compound.
  • the dopant material for example, a fluorescent compound or phosphorescent compound.
  • the compound for the EML layer (host plus dopant) generates visible light colors.
  • Hole injection layer refers to a layer in an electroluminescent (EL) device, which functions to transports holes from the anode to the hole transport layer (HTL) or emitting material layer (EML) .
  • the hole injection layer is typically formed, on the anode, from an aromatic amine or diamine.
  • HTL Hole transport layer
  • HIL hole injection layer
  • EML emitting material layer
  • the HTL compound is also used to help block passage of electrons transported by the emitting material layer (EML) . Small electron affinity is typically required to block electrons.
  • An HTL compound (e.g., of Structure 1) should desirably have a larger triplet energy to block exciton migration from an adjacent emitting material layer (EML) .
  • EML emitting material layer
  • conventional HTL compounds include aromatic tertiary amines (e.g., an arylamine) , for example, di (p-tolyl) aminophenyl] cyclohexane (TPAC) , N, N-diphenyl-N, N-bis (3-methylphenyl) -1, 1-biphenyl-4, 4-diamine (TPD) , and N, N'-diphenyl-N, N'-bis (1-naphthyl) - (1, 1'-biphenyl) -4, 4'-diamine (NPB) , among others
  • aromatic tertiary amines e.g., an arylamine
  • TPAC di (p-tolyl) aminophenyl] cyclohex
  • substrate refers to a support for an electroluminescent (EL) device (e.g., an OLED) .
  • EL electroluminescent
  • Nonlimiting examples of substrates include a silicon wafer, a quartz or glass plate, a metal plate, a metal foil, a plastic film or sheet (e.g., a polymeric resins such as polyester, polymethacrylate, polycarbonate, polysulfone, among others) .
  • GC-mass spectrometry was performed on a HP 6890 series GC system with a "12 m x 0.2 mm x 0.55 ⁇ M" DB-MS column (coiled) .
  • Routine LC/MS studies were carried out as follows. Five microliter aliquots of the sample, as "3 mg/ml solution in THF, " were injected on an AGILENT 1200SL binary gradient, liquid chromatography, coupled to an AGILENT 6520 QTof, quadruple-time of flight MS system, via a dual spray electrospray (ESI) interface, operating in the PI mode.
  • ESI electrospray
  • DSC Dynamic Chemical Vapor Deformation
  • the sample (about 7-10 mg) was scanned from room temperature to 300 °C, cooled to –60 °C, and reheated to 300 °C.
  • the glass transition temperature (T g ) was measured on the second heating scan.
  • Data analysis was performed using TA Universal Analysis software. The Tg was calculated using the "mid-point of inflection" methodology.
  • Table 1 lists the electronic properties (energy of HOMO, LUMO and T 1 in eV) of the most preferred molecules (See pages 4 and 5 above. ) .
  • inventive compounds can be synthesized, in part, by using the following: standard Grignard chemistry, metal-mediated coupling of aryl halides with organo-boron reactants and amines, or a combination thereof.
  • the inventive compounds can be used as charge transporting layers (e.g., HTL and/or ETL layers) and other layers in an OLED device, for example, as emission layers, charge blocking layers and charge generation layers.
  • a 0.5 L round bottomed flask was filled with toluene (300 mL) .
  • the flask was then charged with indole compound (19) (15. g, 67.0 mmol) , CuI (12.76 g, 67 mmol) , K 3 PO 4 (28.452 (134 mmol) , and the diamine compound (N, N'-dimethyethylenediamine) (10.82 mL, 100 mmol) .
  • the mixture was stirred and iodobenzene (20) (15 mL, 134 mmol) was added.
  • the flask was fitted with a Stevens condenser and was refluxed for 3 days.
  • OLEDs were fabricated onto an indium tin oxide (ITO) coated glass substrate that served as the anode, and topped with an aluminum cathode. All organic layers were thermally deposited by chemical vapor deposition, in a vacuum chamber with a base pressure of ⁇ 10 -7 torr. The deposition rates of organic layers were maintained at 0.1 ⁇ 0.05 nm/s. The aluminum cathode was deposited at 0.5 nm/s. The active area of the OLED device was "3 mm x 3 mm, " as defined by the shadow mask for cathode deposition.
  • ITO indium tin oxide
  • N1, N1'- ( [1, 1'-biphenyl] -4, 4'-diyl) bis (N1- (naphthalen-1-yl) -N4, N4-diphenylbenzene-1, 4-diamine) was evaporated at a constant 1 Angstrom/second (A/s) rate, until the thickness of the layer reached 600 Angstrom.
  • the HTL compounds were evaporated at a constant 1A/srate, until the thickness reached 200 Angstrom.
  • N4, N4'-di (naphthalen-1-yl) -N4, N4'-diphenyl- [1, 1'-biphenyl] -4, 4'-diamine (NPB) was used as a reference material for the HTL material to compare with the inventive compounds 1 (a) and 2 (a) .
  • J-V-L current-voltage-brightness
  • KEITHLY 2308 source measurement unit
  • MINOLTA CS-100A luminescence meter
  • Inventive Compounds 1 (a) and 2 (a) were each further purified by sublimation, and incorporated into OLED devices for preliminary evaluation against the reference compound (NPB) .
  • OLED devices were fabricated, as discussed above, on coated glass substrates with multiple organic layers sandwiched between a transparent ITO anode and an aluminum cathode.
  • Table 3 shows the OLED device testing results of inventive Compound 2 (a) mixed with Liq (50: 50) compared to the reference compound (NPB) .
  • the devices containing the inventive compound had better (higher) efficiency and better (lower) operating voltage over the device containing the reference compound.
  • Nit candela per square meter (Cd/m 2 )
  • alkyl groups in addition methyl, will also show good electrochemical reversibility.
  • Such groups include, but are not limited to, linear or branched C1-C6 alkyls, and preferably include ethyl, propyl, n-butyl, i-butyl, and t-butyl.

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Abstract

La présente invention concerne une composition comprenant un composé choisi à partir de la structure 1, comme décrit ici :
PCT/CN2015/098252 2014-12-29 2015-12-22 Compositions comprenant des indoles 2, 3-disubstitués comme matériaux de transport de charge, et dispositifs d'affichage fabriqués à partir de celles-ci Ceased WO2016107459A1 (fr)

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KR1020177018722A KR20170100552A (ko) 2014-12-29 2015-12-22 전하 수송 물질로서의 2,3-이치환된 인돌을 갖는 조성물, 및 이 조성물로부터 제작된 디스플레이 장치
EP15875137.0A EP3240776A4 (fr) 2014-12-29 2015-12-22 Compositions comprenant des indoles 2, 3-disubstitués comme matériaux de transport de charge, et dispositifs d'affichage fabriqués à partir de celles-ci
CN201580068921.4A CN107406382A (zh) 2014-12-29 2015-12-22 2,3‑二取代吲哚作为电荷传输材料的组合物和由其制造的显示器件
US15/539,856 US9966537B2 (en) 2014-12-29 2015-12-22 Compositions with 2,3-disubstituted indoles as charge transport materials, and display devices fabricated therefrom

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